General
Preferred name
TECOVIRIMAT
Synonyms
ST-246 ()
TECOVIRIMAT MONOHYDRATE ()
Tecovirimat (monohydrate) ()
ST-246 (monohydrate) ()
Arestvyr, SIGA-246, ST-246, TPOXX ()
ST 246 ()
Tpoxx ()
SIGA-246 ()
ST-246 MONOHYDRATE ()
Tecovirimat siga ()
P&D ID
PD058740
CAS
816458-31-8
869572-92-9
1162664-19-8
Tags
available
drug
Approved by
EMA
FDA
First approval
2018
Drug indication
Virus infection
viral disease
Smallpox
Drug Status
approved
investigational
Max Phase
4.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS
Tecovirimat prevents viral spread throughout the body [F619].; This drug inhibits its molecular target, a protein called p37, from interacting with intracellular transport components necessary for the production of enveloped virus, and therefore the spread of virus [F619].;
TOXICITY
Tecovirimat has demonstrated to be well tolerated, with no serious adverse events (AEs). Common adverse reactions in healthy adult subjects (⥠2%) were headache, nausea, abdominal pain, and vomiting [FDA label], [A35143].; ; Co-administration of repaglinide and tecovirimat may cause mild to moderate hypoglycemia [FDA label].; ; Oral administration of tecovirimat is generally well-tolerated at dose levels up to 2,000 mg/kg/day (mice) [F619].
METABOLISM
In vitro studies indicate that tecovirimat is not a substrate of major cytochrome P450 (CYP) enzymes, but it is a substrate of human recombinant UGTs (specifically of UGT1A1 and 1A4) [FDA label].; ; Tecovirimat was found to be metabolized into 3 most abundant metabolites, M4, M5 and TFMBA, which do not have pharmacological activity [FDA label].
ABSORPTION
Readily absorbed following oral administration, with mean times to maximum concentration from 3 to 4 h [A35133].; A study was conducted to determine the safety, tolerability, and pharmacokinetics of ST-246 administered as a single daily oral dose. Steady state was reached by day 6 (within 3 to 5 half-lives)[A35134].
MOA
Tecovirimat inhibits the production of extracellular viral forms, which are responsible for the systemic spread of infection, inhibiting virus-induced cytopathic effects. Tecovirimat does not inhibit the formation of intracellular forms of the virus (IMV); however, by inhibiting envelopment, and therefore preventing the exit of viral particles from an infected cell, the smallpox infection is slowed to a point where the immune system can eliminate the virus [F619].; ; Tecovirimat has shown a high level of selectivity and specificity for orthopoxviruses. Tecovirimat targets the viral p37 protein, a highly conserved protein with no homologs outside of the Orthopoxvirus genus, inhibiting its function that is necessary for required for the viral envelopment of IMV (intracellular mature virus). Tecovirimat interferes with the cellular localization of p37 viral protein and prevents its association with cellular proteins involved in membrane trafficking [F619].
DESCRIPTION
Tecovirimat (ST-246) is an orally bioavailable and selective compound against orthopoxviruses including vaccinia, monkeypox, camelpox, cowpox, ectromelia (mousepox), smallpox and variola viruses. Tecovirimat is evaluated against vaccinia, cowpox virus, ectromelia virus with EC50 values of 0.01 ¦ÌM, 0.48 ¦ÌM and 0.05 ¦ÌM, respectively. Tecovirimat targets the orthopoxvirus protein VP37 which is necessary for membrane envelopment of intracellular mature virus particles to form enveloped virus. Tecovirimat exerts antiviral activity on the target of the cowpox virus V061 gene, which is homologous to vaccinia virus F13L, encoding a major envelope protein (p37) required for production of extracellular virus[1][2][3][4][5].
DESCRIPTION
Tecovirimat (ST-246) monohydrate is the monohydrate form of Tecovirimat (HY-14805). Tecovirimat monohydrate is an orally bioavailable and selective compound against orthopoxviruses [including vaccinia, monkeypox, camelpox, cowpox, ectromelia (mousepox), smallpox and variola viruses]. Tecovirimat monohydrate is evaluated against vaccinia, cowpox virus, ectromelia virus with EC50 values of 0.01 ¦ÌM, 0.48 ¦ÌM and 0.05 ¦ÌM, respectively. Tecovirimat monohydrate targets the orthopoxvirus protein VP37 which is necessary for membrane envelopment of intracellular mature virus particles to form enveloped virus. Tecovirimat monohydrate exerts antiviral activity on the target of the cowpox virus V061 gene, which is homologous to vaccinia virus F13L, encoding a major envelope protein (p37) required for production of extracellular virus. Tecovirimat monohydrate could be used in the study for orthopoxvirus-induced diseases[1][2][3][4][5].
DESCRIPTION
Tecovirimat (ST-246) is a core protein cysteine protease inhibitor with potential for the treatment of smallpox infection. Tecovirimat is a novel antiviral agent with potent and selective activity against a variety of orthopoxviruses (EC50 values of approximately 10 nM). Tecovirimat can inhibit orthopoxvirus egress by targeting the viral p37 protein ortholog.
(TargetMol Bioactive Compound Library)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
0
Organisms
4
Compound Sets
14
ChEMBL Approved Drugs
ChEMBL Drugs
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
NCATS Inxight Approved Drugs
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
31
Molecular Weight
376.1
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
1
Rotatable Bonds
2
Ring Count
6
Aromatic Ring Count
1
cLogP
2.4
TPSA
66.48
Fraction CSP3
0.42
Chiral centers
6.0
Largest ring
6.0
QED
0.64
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
Cysteine Protease
Arenavirus
Orthopoxvirus
Antiviral
Indication
smallpox
MOA
orthopoxvirus egress inhibitor
Pathway
Anti-infection
Proteases/Proteasome
Source data
